Buying Your First Iconic Luxury Watch? - 10 Best Value Under $5000: Tudor, Omega, Grand Seiko & More

Today I share my list for the best value iconic luxury watches under $5000 for 2023. I discuss how to find them, tips for bargain sweet spots online when buying new, used, or vintage, and if you are considering buying your first luxury watch, why you can't go wrong with this list of my 10 favorite brands. Whether you’re after a technological innovator or a design, cinematic, cultural or horological icon, there's something for everyone in this video. And while I could have nominated hundreds of watches, I wanted to keep this video short, so please share your own favorites when it comes to the best value iconic watches in the comments.
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Top 10 Best Dive Watches Under $500:
• Our Top 10 Best Dive W...
The Hidden Meanings of the Luxury Watch:
• The Power, Secret Mean...
Essential Watch Movements Explained:
• Understanding Essentia...
Cartier Santos Review:
• This Cartier Watch Is ...
Panerai Luminor Review:
• My First Panerai Watch...
***SPOILERS AHEAD***
Watches featured in this video: The Classic 1950s Omega Seamaster, vintage Deville, new and 90s Brosnan James Bond era Seamasters, both the Omega Speedmaster automatics and Professional "Moon Watch". Tudor Black Bay, Ranger, Prince Oyster Date-Day, Submariner and Hydronaut. The Breitling Navitimer, Cosmonaut and Aerospace, along with the Sinn 903 version of the Navitimer. The Hanhart 417 ES and 417 Flyback version. The Max Bill collection from Junghans, including the Chronoscope chronograph. The Frederique Constant Classic Worldtimer Manufacture and its newest 2023 update of the Worldtimer for their Highlife collection. The Cartier Santos Galbee and Tank XL. The Panerai Luminor PAM048 40mm and larger 44m variations. The Grand Seiko with the SBGW283 from their nature inspired "Elegance" collection. Honorable mentions include the Girard Perregaux Richeville and IWC Mark XVIII Flieger watches.
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Thank you for watching The Urban Gentry channel, home of the #wristwatchcheck and #seikosaturday! Check out my other videos for more watch and lifestyle content.
#watchcollector #top10 #luxury #omega #tudor #breitling #hanhart #frederiqueconstant #cartier #grandseiko

[@tylerbishop4811]

It’s a great list! I’d also include Longines. Few brands in that price range can match their heritage and quality. They truly have something for everyone. I own their Heritage Military and it’s one of my favorites

[@vktravellog1242]

Longines is a great one!

[@nash9625]

My wife's favorite is a longines moon phase, great watch and really well done and accurate. I really like that Zulu time but for some reason can't get past the stars, really like the brand though

[@BC1878]

I’ve just purchased my first Longines and it won’t be my last. I adore it.

[@CymInUA]

Longines also seems to be a brand on the up these days.

[@sniskan85]

Love my Longines (Spirit)

[@fredo1070]

Modern Tudor is killing it, what Rolex was like in the 1960s. A good tool watch with great specs, expensive, but not obscene.

[@RedimAmeti]

I feel like I’m in the minority, but I’ve come to really value having a date complication on my daily wear tool watches. And unfortunately Tudor only has date complications in their more bulky offerings. If they ever made a BB58 sized watch with a date complication, that would be fantastic.

[@rabtrekker]

I second you with the date complication, which would be best at 6. Then address the ghastly snowflake, change it for something more elegant.

[@conorholloway2341]

​@@rabtrekker i think the snowflake is what makes tudor stand out and i think its just very classy

[@Roomfulofgear]

@@RedimAmeti check out the Tudor Royal range. Some might say it is too close in DNA to the Rolex Datejust to the point of being a homage, but these fly under the radar and are generally good value second hand. Many sizes available too!

[@mirkosaligari]

@@Roomfulofgear I have a Royal 38mm and a 1926 39 mm and I really like them, good value at a good price.

[@klausm5460]

Nearly impossible to choose a favorite here from Omega Speedy over Sinn to Grand Seiko. But the secret star of the video is the editing. So many cool references and easter eggs, very tempting to watch again right away.

[@jackfoster8344]

Value retention vs investment is such an important distinction. Always found your take on this subject very refreshing.

[@theurbangentry]

🙌🙌🙌 Thank you Jack, I'm glad I am not alone there. Best regards, TGV

[@daneconnelly]

I think Nomos and Longines would be great editions to this lineup.

[@GarrySkipPerkins]

Nomos is nice. I have a Club and really have enjoyed it.

[@robertostefanowicz9749]

I would like to nominate the Cartier pasha as an addition for under 5k one can find many variations used like GMT’s and even opera clock dates and many more. Very underrated watch that looks like no other and directly recognisable with great history

[@chriso5963]

Always refreshing to hear your sugestions and I'm always amazed by your ability to find hidden gems. I was just a bid anoyed by the interruptions but your videos are always top quality.

[@paulsmith1807]

Such a great video. A lot of work, effort, love and passion really goes into your videos. I'm not sure people know just how much time it takes, but you're doing high quality work.

[@dennisthespeedmenace7530]

I’m a Tudor fan and have been for a couple years. I purchased my grail Bb58 a couple weeks ago and have been pleased with the fit on my 6.5 wrist. Love the channel TGV

[@magnusjensen7651]

Really great video, love all the mentioned watches! These videos really gets me in the best watch mood, enjoyable!

[@kristianfurness900]

Love to see that you listen to the gentry and make videos to address our questions. Keep up the great work.

[@joecognac3791]

The Omega Seamaster Aqua Terra is my vote for one of the best values out there, especially compared to Rolex alternatives. Lightly used ones below $5k are available. Another great video TGV.

[@theurbangentry]

Thank you Joe 👏👏👏 Outstanding choice! Best regards, TGV

[@SIZZO76]

The SEAMASTER would be my choice 😊

[@claytonmarkin7863]

I have an AT small seconds, and it’s amazing. Calling it value is weird, but I understand what you are saying for sure. It’s an awesome piece

[@nash9625]

Really wish they would figure out a micro adjust for that bracelet, the AT is so versatile though, looks great on the rubber or leather.

[@TRUYORK718]

​@@SIZZO76 seamaster aquaterra

[@ExpeditedProductions]

As said previously, Longines. Definitely should make the list. Tudor is my number one. It surpasses so many pieces at the same price point even if the “Black Bay” line up is getting a redundant. What is funny to me is that everyone pushes for smaller pieces, I actually like the original 41mm “slab sided” originals. The original heritage line will always be iconic yet modern. Love FC! I also have been looking to add one to my collection. Can’t decide over the Highlife line or a more classic piece. They are exquisite! Excellent smorgasbord of options, TGV. Thank you, as always. Onward and upward, my friend!

[@brianF584]

Great video TGV, good discussion. Was lucky to purchase a SMP 300 blue dial blue strap combo. Its my dream watch since Goldeneye, first luxury watch and my one and done. Love it, makes me smile everyday. Keep up the content!!

[@NeoRazor]

My first true luxury watch was one I just received this past Christmas. A Tudor Pelagos in black. It's done what I thought no watch ever could--become the only watch I ever wear anymore. Too much text on the dial? I love it. The matte black ceramic bezel, the amazing crispness of an all-titanium watch, the sharp edges, the endless versatility...it's a watch that scratches all my itches. The fact that it's not an 'iconic' watch you see in lots of movies actually makes it more attractive to me. This isn't James Bond's watch, it's mine.

[@daniell2217]

Thank you for getting back to what you do best.

[@fabiolombardo2914]

Grazie per questo video! One can always learn something new from your videos… Fantastic job!

[@THEMADWATCHCOLLECTOR]

Great list my friend!!!! I would also say Longines! Love their heritage range. Maybe always make their watches 2 to 3 millimetre’s too big but their military history and reinterpretations are sweet!!!! Still want a Big Eye Chrono! Maybe a tad big but nothing compared to that cockpit Altimeter your still wearing HAHAHA! It’s a beauty really!!

[@zillsburyy1]

OMEGA will always be #1

[@TheShane209]

What a great time for a new video. Just sat down to relax and a new TGV is even better

[@righton1]

Fantastic as always. What a great list.

[@andresantos_]

I’m 18, a when it will be the time, it will be the tudor 1926

[@Javi_C]

Great selections TGV!

[@user-vv1qm5dj9c]

Great list!

[@likelyrain]

Although not exactly luxury Rado, Certina and Longines need more videos made on them, brand awareness in the Western world

[@Christianwpt]

Incredibly well made video & a classy and miscellaneous list! I think a vintage Zenith El Primero might also be a great option in that price range offering a rich history and still being pure class today. Greetings!

[@ricardocastellanoruizdelat9120]

I love your committment to Hanhart. Being a flieger watches´ fan myself it´s a pleasure to find out people like you, who consider horological background above trendy hypes or fashion tendencies. My Pioneer MKI is more valuable to me than any Breitling or Omega I may (and do, indeed) own. Thanks for being so honest and transparent, TGV. By the way, that biography of Erich Hartmann is a hidden treasure, as well... 😉

[@theurbangentry]

🙌🙌🙌🙌 Thank you my friend, I very much appreciate that. O&U! Best regards, TGV

[@CymInUA]

Quite enjoyed that - cheers. :)

[@vktravellog1242]

Love that you mentioned Grand Seiko! Best value in luxury watches! Only thing I do hate is the 9S hi beat as when I store it in my watch roll I see it lose about 3-4 seconds a day! So annoying! If I have it flat I think I get about +1-2 a day. After a month I lost a minute 🤬🤬🤬🤬. I love Grand Seiko but have to share my not so pleasant experience because I expected more. Spring drive is great and I am eyeing on a 9A5 movement because just looking at that design it should be a much more stable watch.

[@charlesdesurne4696]

I have three springdrives , they gain no more than a couple seconds a month , on the wrist .

[@AvgJoeWatchReviews]

Fantastic video. You named most of what I would choose and a few I have never heard of.

[@bmb0y07]

Glad to see another cool video!

[@pavXX]

Great list TGV.

[@MastinoNapoletano420]

Great list TGV! You hit all my favorites! 😂 Spero che tutto sta bene! Thanks for sharing!

[@Zotrax1946]

Brilliant vid! Very tasteful. I own the FC classic, for dressy special occasions. It is beautiful and unique.

[@edmiller873]

Another excellent video! Although a little high in price for my consideration, I'm grateful for TGV's opinion of the higher class of watches. Although, I must say that I have been "looking" into Panerai's offerings more these last couple of weeks.

[@WesolyArek]

Thx for this one.

[@NicholasSpinelli-ej9gr]

Great job good list

[@shamanprime]

Great video. I’d definitely include Longines in the list. Btw, since you often refer to various books, it’d be interesting to see a video about your recommendations for books watch collectors should have. :)

[@fboness368]

👏👏for the rant!

[@evildrmainstream...6767]

absolute banger Gentry

[@davidmulligan42]

Great list! I spent the past couple of years looking for deals on lesser-known watches. Some of my favorites are the like-new Minase Horizon on a bracelet that I found for $1800 (retail was around $5700), the Clerc Hydroscaph Vancouver Bay edition (new old stock) for $1700, and a used, but mint Corum Romulus Power Reserve for $1300.

[@calvinontime]

Frederique Constant has captivated me early on in my watch collecting journey. One of the greatest value watches in the market for some time now

[@donpumsey413]

Great content. I could watch three more hours of this!

[@MisterTurtleTime]

Awesome recommendations TGV! I personally think that the Seiko SLA021J1 is the best luxury dive watch under $5000,-. It has a Zaratsu polished monocoque case, diver's 300m water resistance, and the 8L35 movement. It also a phenomenal modern interpretation of the legendary Seiko 6159 - 7001 high beat 300m diver from 1968. But I got to admit that Tudor is also a great option:)

[@absolutgeist]

Good overview!

[@johnemerson5383]

Wonderful list. Really well curated as usual. I also love the fact that you're not a quartz snob. I have Omega, Breitling, Longines and Tissot, all in quartz. The only auto I have is a Tag Heuer Caliber 7 GMT and I think that might be going soon to be replaced by the iconic Timex GMT.

[@johnviano4584]

Hi TGV, thanks for the video. Always nice to see you wearing Lacoste. It's been my favorite polo since childhood. Every time you show your vintage Omega Seamaster, I smile, because it reminds me of my 1955 Seamaster which I have loved for the past 8 years. Always nice to see your videos my friend. Have a great week. Best regards, John

[@theurbangentry]

Thank you John, you know, that polo and the Seamaster is perhaps as good as it could ever get. You are always a man of great taste, grazie mille John. Un abbraccio! T.

[@MrDominicharrison]

What a surprisingly great list! That GS is just gorgeous and thank you for introducing Hanhart! Zeppelin is worth a mention

[@mikefleissner4415]

Thanks.your Tudor sub is still my favorite

[@A.Oonthebeat]

great video as always

[@DustandPiers]

Damnation. I had just gotten the anthracite dial Max Bill out of my mind! Great episode, good to highlight the "tale of two tudors," too. There are some gems out there for those interested in going beyond the contemporary iteration.

[@lshin80]

Seiko Marine Master 300. Not yet as iconic as its Rolex and Omega counterparts, but destined to future legend status, and currently the best buy in the luxury divers category. Also, Omega is rumored to release a reissue of the iconic 1960's Seamaster 300 big triangle... much likely over 5k, but an absolute killer.

[@lonewolfemcquade8133]

Roger Moore wore a Seiko tuna Marine master in the James Bond film For your eyes only 1981 so it's definitely iconic. Even the 7C46 movement in the Tuna Marine is LEGENDARY

[@MrTrip3r]

Awesome content! Massive respect and admiration of your job! May I ask a recommendation where I could find a reliable auction site to buy watches?

[@joanjo8465]

Great video and selection. A greeting from Spain. I also found Longines at fault. Great legacy and history with this brand as well as excellent value for money. Thank you very much for your excellent reviews, which I am following with great anticipation.

[@rockymountaindt8410]

One of your best! I was among those exclaiming Sinn-my 104 and soon to be purchased U50 are amazing watches. Best - David

[@Nils0scar]

The U50 ticks alot of boxes. Haven't pulled the trigger yet though.

[@straightmanforever69]

Wow nice pieces

[@kubaszewczyk8247]

Excellent video, TGV! It comes at a remarkable time - I recently acquired my grail watch, a mid-1970s Porsche Design 7176S by Orfina, which will be my nomination for one of the best iconic watches/brands in this price category. A watch that needs to introduction, from a brand that has continually produced original and phenomenal designs for over 50 years, not to mention the tie-in with the eponymous car marque. It's certainly not to everybody's taste, but for me that's part of the appeal! I recall you were considering getting one of these design icons, I could not recommend it enough. There is nothing quite like the genuine patina on the lume or the aged, almost gunmetal like PVD finish on the case and bracelet. This one ain't leaving my wrist anytime soon. Regards, K.

[@Trapvision3D]

This is very educational. You've just thrown me even deeper down this enthusiasts rabbit hole 😂

[@angrypenguin956]

I think that Baum & Mercier could find a spot on that list as well. Quite a few nice pieces to choose from in that price range. I own a Clifton and I think it's an exceptional value.

[@HRM.H]

One that has to be mentioned is the Reverso. Such a iconic and versatile piece.

[@theurbangentry]

YESSSSS!!!! I had no idea you could get them under 5k, I am deffo going to look into that, thank you Thomas, Best regards, TGV

[@HRM.H]

​@@theurbangentry can get them pre owned for very reasonable prices!! Sometimes around 2000 USD.

[@theurbangentry]

Whaaaaaat?!?!?! You are going to get me into trouble my friend! 🤣🤣🤣

[@antcob727]

Don't tell him, he will ruin it for us! 😂 ( remember the geneve microrotor?)

[@terryl7749]

You just added Urban Gentry tax on to the Reverso

[@barryvercueil2346]

Incredible list. Definitely for us Enthusiasts. I honestly look for ETA movements in used watches because of the ease of repair or replacement. Cheers.

[@jroobz]

speaking from personal experience, my first and only luxury piece is the Tudor BB58. I'd recommend that

[@theurbangentry]

👏👏👏 Thank you Josh, I don't blame you, pure class all the way. Best regards, TGV

[@dennisthespeedmenace7530]

I’m with you all the way with the Tudor bb58. Just received mine two weeks ago and take it off my wrist.

[@heikowallauer]

Good evening TGV, that IS a great list you curated here with a lot of potential for future purchases. Personally I'm on the journey towards my next purchase. Let's See what I will end up with. Hanhart is defo on my list. Best regards!

[@theurbangentry]

🙌🙌🙌 Hanhart should be on everyone's list! Thank you my friend, have a great rest of your weekend. Best regards, TGV

[@oklahomahank2378]

I have no desire for a luxury watch, but I enjoy hearing you discuss them. Most of my watches are G shocks. My hobbies are fishing, shooting, and motorcycles, so I need a tough watch. I have a Junghans Max Bill for dressy occasions.

[@chrispatterson8210]

Great video. Love the intro song. I would like to hear more about Zenith - more specifically the El Primero Sport Chronomaster.

[@theurbangentry]

So funny you mention that, I am considering buying one as we speak. I will share more in a future video. Thank you Chris, great minds obviously 😉🙏 Best regards, TGV

[@P27520]

I'd pick Omega. Awesome video, as always!

[@MrTimsfilms]

Love to see a video detailing how you search for a new pre-owned/vintage piece.

[@lonewolfemcquade8133]

My first watch was a Seiko Speedmaster from the early 80s and my first luxury watch was a Breitling Chronomat Blackbird. I wish I still had both of them

[@nonyabiz5326]

Hi. Just bought my first luxury watch under 5k, but did it before I watched this. Seiko Landmaster Springdrive SBDB005. I LOVE it. So glad I finally spent the money and got what I wanted. So glad I didn't cheap out.

[@anthonynigelkendrick5474]

My first timepiece was a Raymond wail GMT. & I still remains one of my favorite timepieces.

[@whiteknight8495]

My first jump into luxury watches in the price range was the Tag Heuer Formula 1 Senna recently released 2021-2022. Great video TGV!

[@manueljnegrete5048]

TVG, I have multiple Omegas and Tudors in my possession. I have finally gotten over the word Seiko in GS. I feel that GS would have had a much easier time if they had gone to the name Credor or something. Long story short, I sold a Bond era Seamaster and a triple date Speedmaster to aquire a new GS sbgm221 gmt and received it yesterday. The workmanship is just stunning. I am firmly convinced that GS has turned the corner and will be a real force to recon with. It is unbelievable what GS has available for so few relative dollars.

[@andyholton7959]

The GSeiko looks beautiful 👌🏻

[@jeremycorrao]

Great video! I don't think you can beat Grand Seiko as far as quality and craftsmanship. Not many brands can compete. Cheers!

[@johnbonanni1731]

TGV your video introduction is the best! I think another introduction to luxury watches in my opinion is the Oris. Cheers!

[@theurbangentry]

👏👏👏👏 YESSSSSS, love Oris, thank you John, deffo number 11 after my top 10. Best regards, TGV

[@ruuddierking8595]

I would always recommend new and vintage Longines watches. I own a Master collection day date and I absolutely love it 👌 Keep up the good work TGV💪

[@travr6]

I just bought that gold and steel Santos. Absolute perfection

[@andrewhennessy9789]

My 1st luxury watch was a Quartz Omega SMP 300. I still own it & love it.

[@zander4517]

Great to see Hanhart get a mention here. I need to pick one up before the world finds out about them and prices go up!

[@Bushdad89]

F##$ man top notch content and style, a channel for enthusiast's 👌 "especially if you go quartz, nothing wrong with that." I love that, I've had a bit of shift to quartz lately and I love them, it's just nice to put it on your wrist without the faff.

[@BC1878]

I’ve just bought a Longines Conquest V.H.P and I’m in love with it. Just touching £1000 but worth every penny. I’m already eyeing my next one, think it’s going to be the Tissot PRX powermatic80. I think it’ll be the watch I wear on my wedding day which is fast approaching. Love the content TGV, keep’em comin.

[@george88pizza43]

Congratulations, hope the wedding goes well!

[@mattys1467]

Hard to argue with any on that list. I would personally have Omega and GS at the top. I would also give a strong honourable mention to the Ball Worldtimer as a competitor to the FC. With any in and around that price category, I would most certainly go pre-owned, so much value to be had.

[@zambonidriver42]

TGV, fantastic material! As top 10’s go, you crack me up. It’s never just a top 10, it’s a journey, with a few left turns, a few right turns, and more than a few stop signs.

[@martinharrison4245]

Hi T, i bagged a tudor aeronaut GMT with bracelet for under 2k . Its 41mm but only 10.5mm thick, and feels like a true luxury watch. I have the bb41 in s and g , and although its a chronometer, and keeps amazing time, the older tudor is streets ahead in class, and really has the rolex DNA. I also have a old rado original diver, and the construction is just amazing. Tungsten carbide bezel, ss bracelet with a titanium clasp. Rado really are fantastic watches , that know how to combine the best materials. The captain cook range are great value , and rado as a whole are a very underrated brand. Whilst i havent experianced a grand seiko, i have got a sla043, the 62mas, and its got to be bordering on that same level, because its a gorgeous diver . I do have a soft spot now for a panerai, they are toolish , but their design are just so cool. Keep up the good work, youve always had a great passion for this hobby , which makes you the best reviewer ive seen , because your love for this hobby shines through. I dont always agree with your taste , as your more military than me , but i do respect the fantastic effort and research that you do in your work. Maybe you should audition for the bond job ? Look at all those fantastic omegas , you could play with and design , lol. Well maybe not bond, as you are a little short, but you would make a brilliant Q !!! Its not just a pen bond , pay attention !!!

[@jupiterjames4201]

Omega 57 is the dream chronograph watch - so incredibly beautiful and comfortable to wear!

[@mariosiaven2965]

I also would mention Nomos amd Longines within this bracket but let me add if I may: Breitling Chronomat, I think it has achieved Ikon status, also, I think you can get a Breguet type 20 within or around the 5k mark in the used market

[@joeshaves1633]

Haha. This video is gonna make me spend some money. But so MANY choices. Pure Class indeed.❤

[@Nachovalenti899]

Omega, Tudor and Longines and my favourites brands.

[@TheBigWrist]

Back in March of 2020 you used to work for WatchBoxx and you had a code for $250 off $5K or more on your channel. I used it to get my first Rolex, OP39 blue for $5250 delivered. I always appreciated that great deal. Thank you.

[@joshuakaplan5726]

loved the GS shoutout with the SBGW 283. I have the SBGW287 Boshu, the burgundy dial. It is a quite a stunner and a total sleeper. Everyone seems to be hype over the classic 231 cream dial or the 283 light blue kishun dial.

[@billyrichardson7237]

I love your Videos Urban Gentry. My first luxury I’d say was my Tudor master chronometer,i I’ve had it for almost a year now, I just got a Rolex blue face all steel white sky dweller. I’d say its hard calling it my Tudor a luxury watch not comparing just saying.

[@Jackie_Treehorn]

I am happy with my Tudor Pelagos 39. Modern, simple und a good watch.

[@stephenlittle7769]

I’ve never purchased a luxury watch. If I ever do, it’d probably be a Tag Heuer Aquaracer or a Grand Seiko.

[@Kylosgrande]

Have you heard of the Mille Miglia by Chopard? I really love it! I’m thinking of getting one if I can find used for good price.

[@lucianofinardi7222]

Great list TGV, as usual. You know, I just can’t get over the feeling that a watch without a date complication does not serve me well. So those options that don’t sport it are automatically out of the list for me.

[@londonerwatches]

Love the vintage Omegas!!!

[@lonewolfemcquade8133]

I actually find vintage Omega designs alot more appealing than modern Omega. Omega Speedmaster Mark 4.5, Mark 3 ,Flight Master, Omega Seamaster big triangle, Soccer ⚽️ time chronograph are awesome 👌 Pie pan Seamasters. Just alot of fascinating pieces

[@thomasforinger3488]

Great Choices. Missing a Universal Polerouter De Luxe Gold , Microrotor... fantastic dials out there.

[@asiantimepieces]

I’d pick Omega or Tudor, but all of them are stunning options.

[@indianasunsets5738]

Great list! I would have added Glashutte.

[@Dr_Demographics_IE]

Have to give Nomos a mention, misses the history but has unbelievable heritage coming out of Glashutte and would go toe to toe with watches at much higher price points